86505-48-8

Upstream product

• 147295-36-1 (R)-4-Methyl-2-oxo-4-p-tolyl-cyclopentanecarboxylic acid methyl ester 
• 116384-94-2 (R)-3-Methyl-3-p-tolyl-hexanedioic acid dimethyl ester 
• 90396-60-4 3-p-tolyl-2-(p-tolylsulfinyl)cyclopentenone 
• 86505-47-7 (+)-(S)-3-methyl-2-(p-tolylsulfinyl)cyclopent-2-enone 
• 36553-42-1 ethyl β-methyl-β-(p-methylphenyl)glycidate 
• 33596-66-6 2-(4-methylphenyl)propanal 
• 138371-74-1 4-methyl-4-(p-tolyl)cyclohex-2-en-1-one 
• 138371-75-2 4-methyl-4-para-tolylcyclohexanone 
• 147295-33-8 Trimethyl-((R)-4-methyl-4-p-tolyl-cyclohex-1-enyloxy)-silane 
• 122-00-9 para-methylacetophenone 
• 116384-92-0 (4S,6R)-4-Methyl-4-p-tolyl-6-trimethylsilanyl-oxepan-2-one 
• 116384-93-1 (3S,5R)-6-Hydroxy-3-methyl-3-p-tolyl-5-trimethylsilanyl-hexanoic acid methyl ester 
• 116498-75-0 (3S,5R)-3-Methyl-3-p-tolyl-5-trimethylsilanyl-cyclohexanone 
• 2947-61-7 (4-methylphenyl)acetonitrile 

Downstream Products

• 126892-15-7 2-benzal-4-methyl-4-(4-methylphenyl)cyclopentan-1-one 
• 65564-92-3 (S)-(-)-3-methyl-3-(4-methylphenyl)cyclopentanone 
• 101693-57-6 (R)-(+)-4-methyl-4-(4-methylphenyl)cyclopent-2-enone 
• 126892-14-6 (R)-4-Methyl-2-phenylselanyl-4-p-tolyl-cyclopentanone 
• 105556-86-3 (3S)-5-hydroxymethylidene-3-methyl-3-p-tolylcyclopentan-1-one 
• 105556-87-4 (3S)-5-n-butylthiomethylidene-3-methyl-3-p-tolylcyclopentan-1-one 
• 16196-32-0 (R)-2,2,3-trimethyl-3-p-tolylcyclopentanone 

Relevant academic research and scientific papers

Recoverable polystyrene-supported palladium catalyst for construction of all-carbon quaternary stereocenters via asymmetric 1,4-addition of arylboronic acids to cyclic enones

The development of recoverable catalysts based on the combination of synthetically demanding ligands with transition metals attracts a lot of attention, especially from the environmental point of view. In this paper, we describe the preparation of a recoverable polystyrene supported chiral palladium catalyst based on PyOx ligand suitable for asymmetric 1,4-addition of arylboronic acids to cyclic 3-substituted five- and six-membered enones. In the reaction, all?carbon quaternary stereocenters are formed with a high level of enantioselectivity (up to 91% ee) and conversion (up to 99%). The catalyst was used in 6 cycles with no loss of enantioselectivity and only a small decrease in conversion. A solution of the problems associated with the transition from homogeneous to heterogeneous catalytic systems is discussed.

Catalytic asymmetric total syntheses of (+)-α-cuparenone, (+)-cuparene and (+)-herbertene

A general catalytic asymmetric route to either enantiomers of sesquiterpenes, cuparenes (1–2) and herbertenes (8–9) is disclosed from commercially available 3-methyl cyclopenten-2-one. Following a catalytic enantioselective addition of arylboronic acids to enone 15, compounds 14a-b with all carbon quaternary stereocenters are synthesized in up to 90percent ee in the presence of Pd(II)-PyOx (pyridine oxazoline). Compounds 14a-b are used as precursors for the asymmetric total syntheses of (+)-cuparene (1a) (35percent overall yield in 3 steps), α-(+)-cuparenone (1b) (56percent overall yield in 2 steps), and (+)-herbertene (8a) (34percent overall yield in 3 steps).

Pyridine-Hydrazone Ligands in Asymmetric Palladium-Catalyzed 1,4- and 1,6-Additions of Arylboronic Acids to Cyclic (Di)enones

Catalysts generated by combinations of Pd(TFA)2 and enantiomerically pure pyridine-hydrazone ligands have been applied to the 1,4-addition of arylboronic acids to β-substituted cyclic enones, building all-carbon quaternary stereocenters in high

A chiral pool based approach to antipodes of α-cuparenone

A synthetic route to both antipodes of α-cuparenone was achieved from the readily available chiral pool starting material l-malic acid and involved cyclopentannulation as the key step.

A chiral pool based approach to antipodes of α-cuparenone

A synthetic route to both antipodes of α-cuparenone was achieved from the readily available chiral pool starting material l-malic acid and involved cyclopentannulation as the key step.

Palladium-catalyzed asymmetric quaternary stereocenter formation

An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β,β-disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl2, PhBOX, and AgSbF 6, and provides products in up to 99 % enantiomeric excess, with good yields. Based on this strategy, (-)-α-cuparenone has been prepared in only two steps. Copyright

Construction of a Chiral Quaternary Carbon Center by Enantioselective Deprotonation: Application to the Formal Synthesis of (+)-α-Cuparenone

Construction of a chiral quaternary carbon center was achieved by employing an enantioselective deprotonation with chiral bases and this strategy was applied to the formal synthesis of (+)-α-cuparenone.

ENANTIOCONVERGENT SYNTHESIS OF (-)-α-CUPARENONE INVOLVING CHIRAL INVERSION OF A KETONE INTERMEDIATE

The acid (-)-2 was converted to the ketone (-)-6.Unsaturated ketone (+)-14 was synthesised from (-)-6.The ketone (+)-7 prepared from the acid (+)-3 on 1,2-ketone transposition, furnished the optical antipode (-)-6.

CONSTRUCTION OF CHIRAL QUARTERNARY CARBON CENTERS USING 3-SUBSTITUTED 5-TRIMETHYLSILYL-2-CYCLOHEXENONES: SYNTHESIS OF (+)-α-CUPARENONE

1,4-Addition of Grignard reagents to 3-substituted 5-trimethylsilyl-2-cyclohexenones proceeded in a highly diastereoselective manner.By utilizing the reaction, (+)-α-cuparenone was synthesized starting from enantiomerically pure 3-p-tolylthio-5-(trimethyl